3-Pyridinemethanol → (Pyridin-3-yl)methyl [4-(thiocyanato)phenyl]carbamate

HRID 1659113Notes

Reaction equation

HRID 1659113 reaction equation
[S:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1)[C:2]#[N:3].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=1>C1C=CC=CC=1>[S:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:12])[O:20][CH2:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)[C:2]#[N:3]

Participants

4

Reactant 2

HCID 75103-PyridinemethanolHCID 21527246HCID 21527246, compound

Product 1

HCID 21527248(Pyridin-3-yl)methyl [4-(thiocyanato)phenyl]carbamateYield 47%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of p-thiocyanophenyl isocyanate (5.25g., 0.0298 mole) in 100 ml. of benzene was added 3-pyridyl carbinol (3.25g., 0.0298 mole). An immediate exothermic reaction took place and a solid precipitated. After standing over the weekend 5.5g. of solid was isolated and after recrystallization from toluene this gave 4.0g. melting at 188°-191°C. This was a 47% yield of 3-pyridylmethyl N-(4'-thiocyanophenyl)carbamate.

Workup

  1. customAn immediate exothermic reaction
  2. customa solid precipitated
  3. customof solid was isolated
  4. customafter recrystallization from toluene this gave 4.0g

Sources & evidence

ORD record
ord-92e723a79c5f48e48608af6879aef61a
Source dataset
uspto-grants-1976_06
Patent number
US03966947

Reaction notes

Loading…